Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous Media

In this work, a new catalytic approach for the C-O activation of enol phosphates based on a palladium supported on layered double hydroxide was developed. In this case, two different ketene aminal phosphates were used as models to study the synthesis of α-phenyl enecarbamates N-Boc/CBz under the Suz...

Full description

Saved in:
Bibliographic Details
Main Authors: Jaqueline D. Senra, Aires C. Silva, Raquel V. Santos, Luiz Fernando B. Malta, Alessandro B. C. Simas
Format: Article
Language:English
Published: Wiley 2017-01-01
Series:Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2017/8418939
Tags: Add Tag
No Tags, Be the first to tag this record!
_version_ 1832550699093721088
author Jaqueline D. Senra
Aires C. Silva
Raquel V. Santos
Luiz Fernando B. Malta
Alessandro B. C. Simas
author_facet Jaqueline D. Senra
Aires C. Silva
Raquel V. Santos
Luiz Fernando B. Malta
Alessandro B. C. Simas
author_sort Jaqueline D. Senra
collection DOAJ
description In this work, a new catalytic approach for the C-O activation of enol phosphates based on a palladium supported on layered double hydroxide was developed. In this case, two different ketene aminal phosphates were used as models to study the synthesis of α-phenyl enecarbamates N-Boc/CBz under the Suzuki-Miyaura conditions. The use of an ortho-bromoaniline as precursor allowed the synthesis of the 2-phenyl indole through an arylation/Heck cyclization. Catalyst reusability enabled the synthesis of the heterocycle in moderate yields for four consecutive runs.
format Article
id doaj-art-60db129ba1274c08820083a9b209ee92
institution Kabale University
issn 2090-9063
2090-9071
language English
publishDate 2017-01-01
publisher Wiley
record_format Article
series Journal of Chemistry
spelling doaj-art-60db129ba1274c08820083a9b209ee922025-02-03T06:06:01ZengWileyJournal of Chemistry2090-90632090-90712017-01-01201710.1155/2017/84189398418939Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous MediaJaqueline D. Senra0Aires C. Silva1Raquel V. Santos2Luiz Fernando B. Malta3Alessandro B. C. Simas4Instituto de Química, Universidade do Estado do Rio de Janeiro, 20550-900 Rio de Janeiro, RJ, BrazilInstituto de Química, Universidade Federal do Rio de Janeiro, 21941-903 Rio de Janeiro, RJ, BrazilInstituto de Química, Universidade do Estado do Rio de Janeiro, 20550-900 Rio de Janeiro, RJ, BrazilInstituto de Química, Universidade Federal do Rio de Janeiro, 21941-903 Rio de Janeiro, RJ, BrazilInstituto de Pesquisas de Produtos Naturais Walter B. Mors, Universidade Federal do Rio de Janeiro, 21941-614 Rio de Janeiro, RJ, BrazilIn this work, a new catalytic approach for the C-O activation of enol phosphates based on a palladium supported on layered double hydroxide was developed. In this case, two different ketene aminal phosphates were used as models to study the synthesis of α-phenyl enecarbamates N-Boc/CBz under the Suzuki-Miyaura conditions. The use of an ortho-bromoaniline as precursor allowed the synthesis of the 2-phenyl indole through an arylation/Heck cyclization. Catalyst reusability enabled the synthesis of the heterocycle in moderate yields for four consecutive runs.http://dx.doi.org/10.1155/2017/8418939
spellingShingle Jaqueline D. Senra
Aires C. Silva
Raquel V. Santos
Luiz Fernando B. Malta
Alessandro B. C. Simas
Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous Media
Journal of Chemistry
title Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous Media
title_full Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous Media
title_fullStr Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous Media
title_full_unstemmed Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous Media
title_short Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous Media
title_sort palladium on layered double hydroxide a heterogeneous system for the enol phosphate carbon oxygen bond activation in aqueous media
url http://dx.doi.org/10.1155/2017/8418939
work_keys_str_mv AT jaquelinedsenra palladiumonlayereddoublehydroxideaheterogeneoussystemfortheenolphosphatecarbonoxygenbondactivationinaqueousmedia
AT airescsilva palladiumonlayereddoublehydroxideaheterogeneoussystemfortheenolphosphatecarbonoxygenbondactivationinaqueousmedia
AT raquelvsantos palladiumonlayereddoublehydroxideaheterogeneoussystemfortheenolphosphatecarbonoxygenbondactivationinaqueousmedia
AT luizfernandobmalta palladiumonlayereddoublehydroxideaheterogeneoussystemfortheenolphosphatecarbonoxygenbondactivationinaqueousmedia
AT alessandrobcsimas palladiumonlayereddoublehydroxideaheterogeneoussystemfortheenolphosphatecarbonoxygenbondactivationinaqueousmedia